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How a Killer of his Hedge Fund Dad Went from Privileged Son To Vice and Violnce

August 22, 2016

Two weeks ago, Thomas Gilbert Jr. was sitting in a visitors room on Rikers Island looking like a ghost of his former self: his model blond locks now shoulder length and straggly, his steroid-pumped physique now gaunt, his nails dirty and cut to the quick.

“I haven’t had many visitors,” the 32-year-old Princeton grad calmly told The Post in an exclusive interview. His right hand trembled as he spoke. “I understand why.”

In January 2015, Gilbert was arrested for the murder of his 70-year-old father, Thomas Gilbert Sr.

According to reports, the younger Gilbert, who goes by Tommy, entered his parents’ tony $6,000-a-month Beekman Place rental on Jan. 4 and asked his mother to step out to get him a sandwich and soda. Once she left, he allegedly gunned down his hedge-funder father — for decreasing his monthly allowance from $600 to $400.

Weeks after Tommy’s arrest, a friend from the city visited him at the Manhattan Detention Complex and said Tommy hounded him to help secure drugs from a doctor, as well as a copy of the deed to his parents’ $10 million Hamptons home.

“I didn’t want to assist with that,” the friend told The Post, adding that he cannot recall the name of the pills Gilbert requested.

On Wednesday of last week, the New York state Supreme Court determined that Tommy is fit to stand trial after months of debate surrounding his mental state. At the hearing, Tommy didn’t even glance at his mother, Shelley Gilbert, who is footing the bills for his high-priced attorney.

“This has been very, very hard,” Shelley told The Post the day prior to the hearing. “You do the best you can. It’s like anything else.”

How Tommy went from a life of privilege to being locked up on murder charges is a question still perplexing some of his closest friends. After all, he seemed to have it all.

He grew up in an Upper East Side brownstone. He attended the best schools — Buckley, Deerfield and Princeton — and was a member of the best clubs. He spent his summers surfing on Long Island, where his parents owned a multimillion dollar home in East Hamptons’ exclusive Georgica Association. And he was remarkably handsome.

“He has the pedigree of this incredibly sophisticated person,” says the city friend. “But the mind and the skin are two different things.”

Beneath the well-dressed facade was a painfully introverted man with a history of psychiatric problems and drug use, including LSD and steroids, according to court documents. Despite his $2,400-a-month Chelsea pad and calendar of black-tie benefits, Tommy was unemployed and financially dependent on his parents. Friends say he began to unravel in recent years.

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The late Thomas Gilbert Sr. at the annual Hedge Fund Association Conference in New York in 2014.Photo: AP
He was arrested in October 2013 for assaulting his former Brooklyn roommate, Peter Smith. That following January, he stole a flagpole from Smith’s family’s estate in Sagaponack and returned the next morning, piercing the front door with it. He was charged with petit larceny, though the case was dismissed. According to Vanity Fair, the Smiths wanted to keep the matter private.

A few months later, Tommy was suspended from the Maidstone Club in East Hampton for threatening to kill an employee who found him asleep in the locker room. And in September 2014, when the Smiths’ summer manse was torched by an arsonist, he was flagged as a person of interest by the Southampton Village Police Department.

His then-girlfriend Briana Swanson, who dated Tommy during the summer of 2014, tells The Post that she informed investigators that rags found near the scene matched the purple sheets Tommy had just purchased. No one was ever charged for the crime; the case is still ongoing.

‘It was like watching a car wreck for a year in slow motion.’
– Former prep-school classmate
“Every month you would hear Tommy did something new. And each time it was a little bit more extreme,” says a former prep-school classmate. “It was like watching a car wreck for a year in slow motion.”

One woman, who has known Tommy since she was a child, recalls a first date with him in 2013 at a Brooklyn club.

“The bouncer asked for the cover charge and Tommy looked at me,” she says. “I didn’t have cash.”

“I was like, ‘I’m actually just going to go home.’ ” He insisted on driving her uptown to her parents’ apartment, as he was living on the Upper East Side at the time.

“He said, ‘Why don’t you sleep at my place?’ I was like, ‘No thanks.’ ” He asked again. She refused a second time.

“As we’re driving, he goes past my parents’ street and I was like, ‘Where are you going?’ He said, ‘You’re going to sleep over.’ And then he locked the doors.

“We [were stopped at] one of those long lights and he put the car in park. I knew the child locks go off in park because my sister had the same car,” she says. “So I opened the door and ran out.”

Growing up, Tommy was a parents’ dream.
“He was a star student and a top athlete,” says the prep-school pal. “He did basketball in the winter, baseball in the spring and football in the fall.”

The pal says Thomas Sr. and Shelley “were very effusive about how wonderful Tommy was. Anytime you asked how Tommy was, ‘Oh, he’s so brilliant!’ ”

By the time he enrolled at Princeton, however, the Gilberts’ golden son (the family includes daughter Clare, 26) had strayed off course. He started experimenting with drugs, according to court documents, and seeking psychiatric care.

At the start of his sophomore year, Tommy had a mental breakdown. He holed up in a hotel in Charleston, SC, where he became obsessed with contamination and told his doctor he would ward off people’s germs by giving them the finger from inside his pocket, per the documents.

In 2005, Tommy checked himself into a hospital for insomnia; two years later, he was sent to the emergency room after overdosing on cocaine and psychedelic mushrooms. He was arrested for head-butting an emergency-room worker while high, though charges were eventually dropped. At Princeton, Gilbert came under academic fire for possession of drug paraphernalia and software that he used to hack into other people’s computers, according to court documents. It took him six years to graduate.
Over the last decade, various doctors have diagnosed Tommy with everything from obsessive-compulsive disorder and depression to anxiety and schizophrenia. Court documents reveal a history of mental illness in the family; Shelley’s father jumped out of a fifth-floor window and killed himself.

Yet when the South Carolina doctor tending to Tommy in the early aughts told his parents that he believed their son suffered from schizophrenia, he noted that they seemed resistant to accepting the diagnosis, according to court documents.

Anna Rothschild, a 51-year-old socialite who dated Tommy in early 2014, says he was always at odds with his father.

“His dad was mean to him and constantly put him down,” says Rothschild, who briefly resumed the relationship in December 2014, weeks before Thomas Sr.’s death. “He would call Tommy stupid.”

Tommy’s ex-girlfriend Swanson says the accused killer only ever spoke with his parents about money.

“He would complain about his dad wanting to cut him off,” she says.

When Thomas Sr. died, some expressed shock that his liquid assets only amounted to $1.6 million, given the lifestyle his family enjoyed. A Buckley alum is quick to point out the $4 million equity loan Thomas Sr. took out against the Hamptons house in 2014.

(Tommy’s attorney, Alex Spiro, declined to comment for the article.)

The family friend attended a party four years ago and was shocked to see the Gilberts’ summer home in a state of disrepair.

“The driveway was overgrown, like Grey Gardens,” she says. “Bathrooms weren’t working. There were doorknobs that wouldn’t turn. It was in shambles.”

The 3,700-square-foot house sold in May for nearly $10 million. It was immediately razed.

But the prep-school friend says the Gilberts were just “in a lean period” since Thomas Sr. was trying to get a new hedge fund off the ground. “He could still pay his dues at the River Club,” he says, referencing the chichi private East Side club to which the Gilberts belonged.

Another friend points out that Shelley comes from family money that was not accounted for in her late husband’s tally, and that they had enough wealth (and worry) to retain their current lawyer, Spiro, ever since Tommy’s legal troubles began.

If money was a worry, Tommy didn’t seem in a hurry to fix it. Since graduating Princeton, he had been unemployed, spending days surfing or playing tennis.

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Thomas Gilbert Jr. is escorted out of the 17th precinct in 2015, in New York.Photo: Chad Rachman
In recent years, he told friends he had started a hedge fund called Mameluke Capital and that he had created “his own analytics that were going to be the future,” according to the prep-school pal.

“It sounded like high-frequency trading,” he says. “He was clearly not doing a hedge fund.”

A pal who owns a film company says Tommy lied and told his parents he was working in the movie biz. One day at the River Club, the pal recalls, “his father asked me [about Tommy’s employment]. I told him the truth.”

Some say Tommy is as delusional now as ever.

“He’s in denial,” says the city friend who has fielded phone calls from Tommy since his incarceration. “He thinks he’s at a spa or on vacation.”

When visited by The Post, Tommy was eager to get help from the outside. “Can you talk to any Princeton groups about getting me money?” he asked. He hasn’t taken a job at Rikers because “it doesn’t pay much,” but adds that his mother is providing commissary money.